


A Little Bit of Flip Flopping

by nerdettedrabbles



Category: Supernatural
Genre: Gen, M/M, Return of Gabriel, fem!dean
Language: English
Status: In-Progress
Published: 2014-02-21
Updated: 2014-04-30
Packaged: 2018-01-13 07:46:57
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,116
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1218196
Author URL: https://archiveofourown.org/users/nerdettedrabbles/pseuds/nerdettedrabbles
Summary: <blockquote class="userstuff">
              <p>Dean opened the bathroom door and took a quick peek in the mirror. "See , Sammy? Nothing—" He double took. "What the hell?" There was a girl on the bathroom mirror, but when he turned around, there was no one there. When he raised a hand, the girl in the mirror did too. He stretched, waved his hands around, even did a weird little dance. The girl in the mirror did everything he did. He pulled on his cheeks. He grabbed the girl's hair ends and felt hair. Near his shoulders. His hair was nowhere near that long. One last test. He looked down and... fuck.</p>
            </blockquote>





	1. There Might Be Something Wrong...

**Author's Note:**

> Yo, sporadic updates, sorry about that. Eight million thanks to littlepenguin96 for being an idea well and my editor... sort of... but she's chill and stuff. Love you hun!

Dean woke up really slow, as usual. He stood and stretched, not noticing anything wierd, and slowly walked into the bunker's kitchen. He could hear Sammy up and making breakfast. Smelled like pancakes.

"Mornin', Sammy," he said and went to the fridge to see what they had left over. Didn't look like much. "Need to go shopping again this week." He yawned. "Probably get some pie, too."

Sammy was suspiciously quiet. Dean cast a curious look over his shoulder just to see what Sammy was doing and was greeted with the sight of Sammy pointing a gun at him.

Nothing like a gun pointed at him to wake him up.

"Sammy, what the hell are you doing!?" he yelled, throwing his hands in the air. "Put that thing away before you put someone's eye out!"

Sammy refused to put down the gun. "Who are you, and how did you get into the bunker?"

Dean shook his head. "Haha, good one, Sammy. But I do not look that bad when I get out of bed. I don't have the hair to get bedhead like you."

Sammy adjusted his grip on the gun. "Nice try. Now you have until three to tell me who you are or I shoot."

Dean held up his hands in placation. "Alright, fine. You got me. I'm really a guy named Jim from Canada. Now please put down the gun."

"Three."

"Sammy, come on. Quit playing games and put the gun down."

"Two."

"Sammy! Put the gun down. I'm serious."

"One."

Dean threw his hands in the air. "Quit pretending you don't recognize your own brother, Sammy! It's just me!"

Sammy lowered his gun slowly. "Dean?"

"'Bout damn time, Sammy. I was starting to think I was gonna have to go Bruce Lee on your ass." He went pulled a Red Bull out of the fridge and took a swig.

"Um, Dean?" Sammy looked on the verge of laughing. "Have you looked in a mirror today?"

Dean put his Red Bull on the counter. "No, who do you think I am? The Evil Queen?"

Immediately Sammy doubled over and burst out laughing. "What? Did I say something?"

Sammy stood up and tried to regain his composure, though two seconds later, he was doubled over again. HE waved his hand towards the bathroom, holding his gut. "Just go... go look now.."

Dean rolled his eyes and headed towards the bathroom. "Whatever, Princess." Sammy immediately laughed even harder.

Dean opened the bathroom door and took a quick peek in the mirror. "See , Sammy? Nothing—" He double took. "What the hell?" There was a girl on the bathroom mirror, but when he turned around, there was no one there. When he raised a hand, the girl in the mirror did too. He stretched, waved his hands around, even did a weird little dance. The girl in the mirror did everything he did. He pulled on his cheeks. He grabbed the girl's hair ends and felt hair. Near his shoulders. His hair was nowhere  _near_ that long. One last test. He looked down and... fuck.

"Sammy, what the hell did you do?!" Dean stormed out of the bathroom and got in Sammy's face, though now that he was fully awake, it was incredibly obvious something was off. Sammy was way taller now, there was a bouncy feeling where his... boobs... were, and his voice was a lot higher than normal. Sammy took one look at him yelling in his high pitched girl voice in his tiny little body and fell over laughing. "Sammy, whatever you did, whatever deal you made, fix it. Now!"

Sammy finally managed to sit up and stop laughing for a moment. "Dean, I didn't do anything, I swear. As rich as it is, I wouldn't do this."

Dean rolled his eyes and hopped onto the counter, thanking whatever powers may be that he slept in a shirt and shorts last night. "Riiiight, and I'm the King of Hell. _Don't you dare,_ " he added at the look on Sammy's face.

"I swear, Dean, I didn't do anything. Maybe this is karma for being such a dick to women."

Dean froze. "You saying I'm getting my just desserts?"

Sammy shook his head."I know what you're thinking, Dean, but Gabriel _died_ , remember? It's probably something else. Maybe even a real Trickster."

Of course at that moment there was the sound of the doorbell they installed on the bunker. Sammy stood up. "I got it."

Dean glared at him on the way out. A few minutes later, Dean could hear the door to the bunker opening and... fuck, was that Cas? Before he could make any kind of escape, Cas and Sammy walked back in. Dean gave an awkward wave.

Cas did that funny(adorable) head tilt as he looked at Dean. Then the other way. "Dean, is there any particular reason that you're inhabiting the body of a woman?"

Dean's woman face probably turned into a cherry tomato(damn, women blushed easily!)."I... I, ah..." Sammy, meanwhile, had once again taken up residence on the floor. 

Cas' head tilted again. "You're not intentionally being a woman?"

"Sammy, I swear to God, if you don't shut up I will take your gun and shove it up your ass!" Dean hopped down from the counter. "And no, Cas, I am not intentionally a woman. No man in their right mind would _ever_ choose to be a woman." He stormed angrily into the hall. "Now, if you two eight-year-olds would give me a minute, I'm going to see if Charlie left any clothes here, or I'm not going anywhere!"

~~

"Sammy, I officially hate you."

"Oh, come on, Dean, you know you like it."

"No, Sammy, I'm serious, as soon as I go back to being a man, I'm kicking your ass to the curb. Right after I kick your ass. Repeatedly."

Sammy just laughed. "No, you won't. You don't wanna break a nail."

Charlie hadn't accidentally left any clothes, so Sammy had gone shopping to get something for dean to wear. That something happened to be a pair of  _ridiculously_ short shorts, a flowery top, and (thank God) sneakers. The only problem? The stuff showed off  _way_ more of Dean's new body than he cared to share.  He clenched his hands on the steering wheel. "The only reason I'm wearing this crap is so I can get some jeans and a better shirt."

Cas cleared his throat in the back seat. "I think you look attractive in that outfit, Dean."

Dean's grip on the steering wheel intensified, He could feel a deep blush working its way up his face. Sammy was barely containing himself in shotgun. "Cas, that is  _not_ helpful right now." Dean peeked in the rear view mirror and saw an equally dark flush on Cas' face. Dean shook his head and returned his eyes to the road. "We are going shopping. I am getting a batter outfit, and then we are going  _straight_ to a psychic or something and find out what the hell happened to my body because I am  _not_ staying a woman."

Sammy attempted to make a straight face. "So, uh, Dean."

Dean cast a sidelong glance at him. " _What._ "

Sammy drummed his hands on his thighs. "You know how women are supposed to be worse drivers?"

Dean's grip on the steering wheel was hard enough to turn his knuckles white. "Sammy, you say one more thing, and I—"

"Heeeeello, boys and girl!"

Dean jerked the steering wheel and almost sent the Impala into a ditch. He straightened out and glared into the rearview mirror to yell at Cas. Then he just stared.

Sitting in the backseat next to Cas was Gabriel. Gabriel the archangel. Gabriel the Trickster. Gabriel that killed him over a hundred times on a Tuesday. Gabriel that died fighting Lucifer.

Also apparently Gabriel the incredible douche bag that wasn't dead.

"What the hell, man?! You trying to kill us?" Dean turned his eye back to the road, trying his best to act natural since Cas was apparently incapable of speech and Sammy's jaw was somewhere near the floor.

Gabriel gave an easy smile and spread out in the back seat, pushing Cas into the door. "Nah, just felt like making a sudden visit to my favorite amigos." He winked. "Especially since one makes a helluva good looking girlie."

Dean almost made them crash again. "You...  _you_ turned me into a chick?!"

Gabriel laughed. "Yes, indeed I did! And I must say," he said, taking a closer look at Dean, "I am not regretting it at  _all_ ,"

"Hey! My face is up here!" Dean circled the air around his face. "I  _will_ throw you out of the car."

Gavriel snorted. "As f you in your little body could do that."

Sammy, it seemed, had finally recovered his voice. "Gabriel... you were dead... and you're not now?"

Castiel cleared his throat. "Also, I don't know if you're aware, but Metatron has banished all the angels from heaven, and yet you kept your wings."

Gabriel tossed his hand. "Castiel, as ever, you are the only one to ask the right questions. Let's go on a little field trip to answer it."

"Gabriel, I swear to God, you do anything to this car—"

Poof.

Dean fell flat on his butt, though he was relived to find he was at least in jeans. Also, apparently, a tank top and an open plaid shirt. Finally, something going right.

"You okay Dean?" Sammy walked over and held out a hand to help Dean up. He took it and was hauled to his feet, just making him feel even smaller than usual(damned women and their smallness).

Dean shrugged. "Alright, I guess." He brushed his jeans off and looked around at the forest they were in and froze.

"No, nonononono. Not here. Not here." Dean spun in a small circle and looked around. Right there, the road he walked with Benny to find Cas. There, the mountain. "Goddamned angel took us to Purgatory."

Sam's gaze snapped around, taking in their surroundings. "Shit. You're right."

"Of course I'm right, Sammy. Spent a year here, I'd think I'd know it if I was dropped here out of the blue."

"Dean!"

The Winchesters turned around and saw Cas heading straight for them. "Dean, are you all right?"

Dean nodded, still looking around. "We're back, Cas."

"Welcome to Purgatory, amigos!" Gabriel walked out from behind a tree with his arms open. "And this place is the reason I'm still alive!"

Sammy's gaze was still looking around, as was Dean's. Cas spoke up. "I don't understand. How does Purgatory mean you still have your wings?"

"Because, Castiel, I wasn't on Earth or in Heaven when that spell was cast. Simple enough loophole." Gabriel winked.

Poof.

Back in the Impala on the way to the store.

Dean drummed his fingers on the steering wheel. "Alright. You go to the monster afterlife for a bit, you keep your wings. Now why the hell did you turn me into a girl?"

Gabriel cracked a grin. "Come on, Dean. Yo've always been a princess, now you get to look the part!"

Dean slammed his hands into the wheel. "Damnit, Gabriel! Change me back!"

Sammy turned around a little bit. "Gabriel, I hate to agree with Dean on anything, but he's a lot more bitchy as a woman."

Cas was eerily silent in the back seat.

Gabriel shook his head. "No can do, kiddos. Dean has a lesson to learn. And anyways," he slung an arm around an uncomfortable Castiel, "I'm pretty sure Castiel likes you as a girl."

Both Dean and Cas looked like they were about to explode from embarrassment.

Dean shook his head. "All right, wise guy. What do I have to learn?"

Gabriel shook his finger. "Now, if I told you, where'd the fun be?" And with that, he vanished.

~~

"I'm gonna kill him. I'm gonna kill him." Dean was pacing around the bunker in front of an annoyed Sam and an awkward Castiel(was it just Dean or was he watching Dean's ass?). "I swear to God I'm gonna kill him!"

"That would be unwise seeing as God left a long time ago," Cas said from his perch.

"Not helping, Cas!"

Sammy rubbed his forehead. "Dean, you've been sitting there pacing for three hours and we're no closer to figuring out how to turn you back into a dude. Maybe if you actually think—"

"Shut up Sammy!"

Sam and Cas exchanged looks. "Dean, I'm gonna say something, but don't flip out, okay?"

Dean stopped pacing and turned to face Sammy. "Fine. Go ahead."

Sammy looked really awkward about what he was about to say. "I think you're on your period."

Dean froze for a moment, then fixed Sammy with his most potent bitch face. "Shut up, Sammy. Just shut up. I am  _not_ on a period. Gabriel might be a douche, but he's not that much of a douche."

Sammy looked away. Cas blushed and cleared his throat. "Dean, your um... butt... is covered in blood."

All the blood drained from Dean's face. Frantically he turned in circles. Lo and behold, his ass was entirely red. Slowly he clenched his hands into fists. "GABRIEL, I'M GONNA KILL YOU FOR THIS!!!!!!"

 


	2. Movie Night

**Summary for the Chapter:**

> "Cas, what's this?"
> 
> Cas' cheeks turned a little red. "I, uh... did a little research online about what makes women feel better when they're on their cycle and found a number of results about watching their favorite movies, giving them chocolate, and having them take Advil to help with the cramps..." He rubbed the back of his neck nervously, his cheeks turning red. "I know you're not normally female, but I thought it might still help..."

**Notes for the Chapter:**

> Okay, I gave up. This is gonna be more than one chapter. I can't figure out how to change it to incomplete with it being only one chapter, so we're having a lot of chapters, all of them kinda short but maybe cute like this one :)

~~

"Dean, are you done moping?"

Dean was currently curled up on the couch, wearing a pair of his pajama bottoms and channel surfing.

"Sammy, how many times do I have to tell you that  _I don't mope_?" Nothing good on this channel.

Sammy chuckled. "Okay, then you're sulking."

"I am  _not_ sulking. I'm planning my revenge on Gabriel for freaking turning me into a girl!" Finally, a channel worth watching.

Sammy nodded. "Riiiight. And that's why you're watching...  _The Bachelor..._  with Juan Pablo."

Dean felt his face grow hot. "Shut up, Sammy."  _Click_. "Where'd Cas run off to anyways?"

"I don't know, really. Said he was going shopping."

Dean gave Sammy a skeptical look. " _Shopping?_  He's Cas, he doesn't do shopping. He runs around with a stick up his ass and smites the crap out of stuff."

Sammy checked his phone. "He also doesn't text, and yet here he is, asking me what your favorite movie is."

" _Star Wars,"_ Dean answered without hesitation. "But yeah, that's not like Cas. Shopping." He chuckled.

Sammy took the remote. "Stop watching girlie shows. And stop sulking. Gabriel will change you back once he's had his fun. Just tough it out."

Dean rolled his eyes. "You telling me you'd be okay with it if Gabriel gave you boobs?"

Sammy took a breath. "Yeah, I think so. I wouldn't be reacting like this, that's for sure." He started flipping through channels. "How're the cramps?"

Dean gave Sam a weak glare. "How the hell do you think they are? I'm a freaking dude having  _period cramps_. It's unnatural in every sense of the word." He turned his gaze back to the TV.  _Survivor_. Better that freaking  _Bachelor_.

The Winchesters sat on their couch for a while watching  _Survivor_  reruns. A few episodes in, their doorbell rang, and Sam got up to get it. Dean was glad, because he was pretty sure Gabriel upped his level of douche baggery by giving Dean a woman's period on max which means he may have... overflowed..., so he had a hance to go change.

The sight that greeted him when he returned was strange. Sam was probably in the kitchen getting popcorn, because Cas was standing in the middle of their living room holding a bag full of what looked like chocolate and Advil. He also apparently figured out how to work the DVD player, because the  _Star Wars_ theme was playing.

"Cas, what's this?"

Cas' cheeks turned a little red. "I, uh... did a little research online about what makes women feel better when they're on their cycle and found a number of results about watching their favorite movies, giving them chocolate, and having them take Advil to help with the cramps..." He rubbed the back of his neck nervously, his cheeks turning red. "I know you're not normally female, but I thought it might still help..."

Dean was a little surprised, but somewhere in the back of his head, in a place he didn't normally go, he was really touched. Cas cared enough about him to want to make him feel better about being stuck in a damn woman's body.

Dean could feel his cheeks turning red, and he looked away. "That's... that's really nice of you, Cas. I mean..." What the hell was wrong with him? He couldn't think of anything to say.

Cas seemed to pick up on Dean's uncertainty. "If it was too much, I can always-"

"No!" Dean surprised himself when he blurted that out. "That was... really sweet of you..." Fuck. When did he start calling Cas sweet?

Of course Sam chose that moment to walk in. "Okay, I made a coiple of bags of popcorn, I think that should be enough..." He looked between Dean and Cas. "Is this a bad time? Because I can always just come back..."

"No," Cas said. Dude could stop blushing like nobody's business. Unlike Dean and his stupid lady's cheeks. Damn things turn off and on like they had a mind of their own.

Sam looked again between Cas and Dean. "Ooo-kay. Then let's watch the movie."

~~

Dean wasn't entirely sure when during the movie that it happened. One second he was watching Anekin and Obi Wan duke it out, the next he was leaning on Cas' shoulder.

The only move Cas made was to look briefly at Dean before returning his attention to the screen. Dean let out a breath he didn't even know he was holding and adjusted so he was more comfortable. Maybe being a girl had a few perks he could take advantage of.


	3. Damned Parties

**Summary for the Chapter:**

> Dean was going to murder whoever invented high heels and decided they were mandatory for women to wear to formal occasions.
> 
> He'd been wearing his own pair for something like two hours and still had yet to see anyone from the family.
> 
> Not to mention that shortly after they arrived, some blonde chick came and took Cas away.
> 
> Dean was trying to tell himself he was just annoyed at the fact that Cas couldn't stay focused.
> 
> It wasn't working to well.

**Notes for the Chapter:**

> Holy cow, my story blew up after I changed to chapters, and I got a bookmark! I'm really excited, so I'm going to try and do another update. Not gonna be as cute as the last chapter, sorry, just some rom/com stuff and Dean in a dress.

"Dean, we got something."

Dean looked up from his coffee with a drained look at Sam. He'd had to spend two weeks as a girl so far(thank God he was off that stupid period thing) and had been really lucky to escape having to gank a demon or something. Looks like his luck had run out.

"Alright," Dean sighed, putting down his coffee and looking up. "What do we got?"

"Get this," Sammy said, turning his laptop around so Dean could read the article.

  _Dead Man Found at Sutton Manor_

_Yesterday, Maverick Morgan, 27, was found dead in a locked room at his house in Orlando, Florida. Police are thinking Morgan commit suicide after his girlfriend, Holly Lancer, broke up with him..._

Dean looked up. "I don't see how this is us if this Maverick Morgan offed himself."

"Keep reading," Sammy said, pulling his own coffee towards him.

Dean looked back at the article and started scanning. "Locked doors, slit throat, no..." He rubbed his eyes and took a closer look, reading out loud. "' Morgan had been found in his closet, a large shoe rack pushed in front of the door, and, mysteriously, no sign of the knife that he used to take his own life.' That is a little weird. Okay," he said, closing the laptop, "Let's go see what's going on with Mr. Morgan. You have a plan?"

"Yeah," Sammy said, "but you're not gonna like it."

"Just spill, Sammy."

"Alright. We take Cas and we crash their memorial party."

"Okay, I got no problem with that," Dean said, leaning back in his chair. "We going as bus boys?"

"I am. YOu and Cas are crashing as guests. Which means... you need to wear a dress."

It took Dean a moment to process. And remember he was a fucking girl. So he had to wear a dress either way. "Oh, Hell no. I am  _not_ wearing a dress! I flat out refuse."

Sammy sighed. "Just think about it for a minute. The Morgans are gonna notice two new busboys and a busgirl. Two guests that they don't recognize isn't gonna set off as many warning bells."

"But I have to wear a  _dress_. A fucking dress, Sammy! Do you know how undignified that is? As a man?"

Sammy rolled his eyes. "Do I have to remind you-"

"That I'm a girl right now? No, you don't. But still, man. It's a dress! And I'm me!"

~~

"I fucking hate you, Sammy," Dean growled, pulling the Impala into the parking lot. He wasn't entirely sure how, but Sammy had convinced him to wear a dress. A  _dress_. Sure, it looked good on Dean, but that wasn't necessarily a compliment.

"Just make sure you don't trip wearing the heels and you'll be fine," Sammy said, checking his bow tie in the rearview mirror.

Oh yeah. That was another thing. He was gong to have to wear  _heels_. Heels! A dress, heels,  _makeup_. It was utterly humiliating. He felt exposed. 

"Sammy, you owe me big time," Dean snapped, opening the door and almost falling getting out of the car. Fortunately for him, Cas had already gotten out and was nearby. He caught dean and held onto him for a second while Dean regained his footing.

"Be careful. I hear that those shoes are difficult to walk in," Cas said, though there was a twinkle o humor in his eyes.

Dean would've been willing to put a large amount of money on him turning into a tomato right then, because he had an excellent view of Cas' face, and damn, it was a nice one. It was dark, otherwise he probably would've had an amazing view of some intense blue eyes. As is, he got to stay in Cas' arms really flustered and trying to remember how to stand in heels.

When Dean finally did manage to right himself, he just kinda stood there for a minute. Cas wasn't letting go. But Dean... honestly wasn't complaining.

Sammy cleared his throat. "If, ah, you two are done with the eye sex-" It was almost funny how quick Dean and Cas fixed themselves up. "-we still need to crash the party. I'll meet you two inside."

~~

Dean was going to murder whoever invented high heels and decided they were mandatory for women to wear to formal occasions.

He'd been wearing his own pair for something like two hours and still had yet to see anyone from the family.

Not to mention that shortly after they arrived, some blonde chick came and took Cas away.

Dean was trying to tell himself he was just annoyed at the fact that Cas couldn't stay focused.

It wasn't working to well.

Thank God this party had a bar. Otherwise Dean would have bailed in the first hour. As is, he's probably drunker than he's been at least since that one night with the  shojo. And he had been hella drunk that night.

He was just going for his... twelfth? straight whiskey when a dude sat down next to him. The bartender gave him a warm smile and slid over a beer.

The dude took the beer with a nod before turning his attention to Dean. "Hey there. What's someone like you doing alone at a place like this?"

Dean shrugged, spinning his glass around on the tabletop. "My buddy ditched me," he admitted, picking up his glass and downing it in one go. He was still trying to tell himself that seeing Cas with the blonde didn't bug him.

It still wasn't working.

The guy at the bar nodded sympathetically. "Yeah, me too. Ass ran off at the first sign of boobs." He shook his head and shrugged. "Name's Mark, by the way."

Dean nodded at Mark. "I'm Dean."

"Dean, huh? Interesting name."

Dean shrugged. "Family name. What can you do?"

Mark chuckled. "Yeah, I know the feeling. Twelfth guy in my family named Mark. It's ridiculous."

Dean couldn't suppress his (drunken)grin. "Now  _that_ is the short straw of family names."

Mark laughed. "You're telling me." He finished his beer and slammed the bottle on the counter. "You know what, this stuff down here is crap. I happen to know where they keep the good stuff here. You wanna go get some?"

Dean looked around to see where Cas was. He didn't think he'd be gone long, but he still wanted to let Cas know so he didn't, like, smite everyone here or something. And maybe because he might have maybe wanted to do something. But the little angel was nowhere in sight. "Hell, why not?" He stood up, wobbling a little in his shoes(it's harder to walk in heels when you're a little drunk apparently), and started following Mark. Hopefully the good stuff was really good, otherwise he'd end up stuck drunk on crap.

~~

 

**Notes for the Chapter:**

> Still working on it, my laptop is just about to die

**Author's Note:**

> Hey you little lovelies! I'm really sorry about the irregular updates. I have a weird creative process that hits sometimes and I can turn out crazy amounts of stuff, then I'll go into a huge slump and you won't get updates for a month. I'm really sorry and I'll try to be more regular with m updates! Thanks for sticking with me, and if you have any ideas about what I can do with Fem!Dean, post them in the comments! You never know, I might use them!


End file.
